Home Physical Sciences The crystal structure of 2-acetylpyridine-ortho-fluoro-phenylhydrazone, C14H12FN3O
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The crystal structure of 2-acetylpyridine-ortho-fluoro-phenylhydrazone, C14H12FN3O

  • Qutaiba Abu-Salem ORCID logo EMAIL logo , Haitham Al-Sa’doni and Helmar Görls
Published/Copyright: May 7, 2025
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 240 Issue 4

Abstract

C14H12FN3O, monoclinic, P21/n (no. 14), a = 7.4339(2) Å, b = 19.1864(5) Å, c = 8.6861(3) Å, β = 105.705(1)°, V = 1192.65(6) Å3, Z = 4, R gt (F) = 0.0367, wR ref (F 2) = 0.0486, T = 133(2) K.

CCDC no.: 2448116

The molecular structure is shown in the figure. Table 1 contains the crystallographic data. The list of the atoms including atomic coordinates and displacement parameters can be found in the cif-file attached to this article.

Table 1:

Data collection and handling.

Crystal: Colourless prism
Size: 0.13 × 0.12 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.10 mm−1
Diffractometer, scan mode: Bruker APEX2, φ and ω scans
θ max, completeness: 27.1°, 100 %
N(hkl)measured, N(hkl)unique, R int: 8338, 2626, 0.049
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2,283
N(param)refined: 220
Programs: Bruker, 1 , 2 , 3 SHELX 4 , 5

1 Source of materials

The Schiff base was prepared by mixing equimolar amounts of 2-acetyl-pyridine (10 mmol, 1.21 g) with 2-fluoro-carboxylic acid hydrazide (10 mmol, 1.54 g) in ethanol. The mixed solution was refluxed for 3 h and then was cooled to ambient temperature. The solvent was evaporated under reduced pressure to produce the final compound which was crystallized from ethanol-chloroform (1:4 V/V) as colorless prism-shaped crystals. 1H NMR (DMSO‑d 6): δ (ppm) 1.9 (3H, CH3), 7.28–7.32 (4H, m, Ph), 7.56–7.62 (4H, m, PY), 9.97, 10.1 (1H, d, NH (N–H⋯F)); 13C NMR (DMSO‑d 6): δ (ppm) 21.1, 116.63, 116.84, 122.74, 122.89, 125.05, 125.27, 130.62, 133.39, 133.48, 158.49, 160.97, 163.52, 168.68. Anal. Calc. for I: C14 H12FN3O (%) (Mr = 257.27): C, 65.36; H, 4.70; N, 16.33. Found: C, 65.34; H, 4.68; N, 16.32.

2 Experimental details

All chemicals and solvents were used as purchased without further purifications. The high resolution NMR spectra were recorded at room temperature in DMSO‑d 6 solution by a Bruker DRX 400 NMR spectrometer (1H 400 MHz; 13C 100 MHz, using TMS as external standard). The intensity data for the compound were collected on a Bruker–Nonius Kappa–CCD diffractometer equipped with a MoKα IμS microfocus source and an Apex2 CCD detector. Data were corrected for Lorentz and polarization effects; absorption was taken into account on a semi-empirical basis using multiple-scans. 1 , 2 , 3 The structure was solved by Direct Methods (SHELX 4 ) and refined against Fo 2 (SHELX-2018). 5 All hydrogen were located by difference Fourier synthesis and refined isotropically. All non-hydrogen atoms were refined anisotropically. 5 MERCURY 6 was used for structure representations.

3 Comment

Acylhydrazones, (–C(O)–NH–N=CH–), and their metal complexes have been proved to possess biological activity, antioxidant activity, luminescent properties and catalytic properties, which makes the study of this class of compounds receive considerable attention. 7 , 8 , 9 , 10 , 11 , 12 Non-covalent interactions such as hydrogen bonding, π⋯π stacking and C–H⋯π interactions could be employed to assemble interesting supramolecular networks of some hydrazone ligands and their metal complexes. 8 , 12 , 13 , 14 Therefore, in continuation to our interest in acylhydrazones and supramolecular chemistry, we have explored the involvement of H-bonds, halogen bonds (e.g. X⋯X and C–H⋯X (X = halogen) and π⋯π) interactions between aromatic systems in the formation of supramolecular assemblies of new fluorinated phenylhydrazone compounds. We believed that the existence of F atom would increase the acidity of the C–H aromatic ring, promoting its role in H-bonds and the formation of π⋯π stacking interactions assisted by halogen bonds (X⋯X), which are not observed in similar compounds. 15 , 16 , 17 , 18 , 19 , 20 From this perspective, the crystal structure (see top part of the figure, 50 % probability ellipsoids) of a new fluorinated acylhydrazone compound, derived from the condensation reaction of 2-acetyl-pyridine with 2-fluoro-carboxylic acid hydrazide is reported, was explored to understand the role of halogen-based bonds in building new mixed “phenyl pyridyl” embraces in its supramolecular architecture.

The bond distances and angles of the Schiff base molecule of the compound fall in normal ranges. 8 , 15 , 16 , 17 , 18 , 19 , 20 The crystal structure exhibits intramolecular hydrogen bond between the hydrazone N–H group and the F atom, N1–H1⋯F1 [1.982(1) Å, 134.97(3)°], and forms the six-membered ring motif (see top part of the figure). The molecule is twisted with dihedral angle between the pyridine and the fluorinated phenyl rings of 2.93(5)°.The molecule has a trans configuration with respect to the methylidene unit with torsion angle C6–N2–N1–C7 of 177.73(1)°. The double C6–N2 bond [1.290(2) Å] is within the normal range of similar compounds, 8 , 16 , 17 , 18 , 19 , 20 . The N1–C7 bond [1.366(2) Å] is significantly longer than the double C6–N2 bond, which is expected for sp 2-hybridized C–N bonds, indicating conjugation over the hydrazone moiety. The carbonyl oxygen atom is deviated [0.410(1) Å] out of the mean plane passing through the fluorinated phenyl, pyridine rings and the acylhydrazone group, as a result of weak intermolecular hydrogen bond interactions as discussed later on.

The supramolecular self-assembled structure formed through C–H⋯N intermolecular hydrogen bond between the azomethine –C=N–N– and the methyl groups, resulting in symmetrical R2 2(8) rings. π⋯π stacking interactions are observed between the fluorinated phenyl…pyridine rings connected the centrosymmetric molecules into dimers with centroid-to-centroid distance being 3.692(2) Å and with an inter-plane angle of 2.934(3)°. Each centrosymmetric dimer is further connected via longer stacked interactions [3.783(1) Å; −x, 1 − y, 1 − z] leading to chains of stacked molecules along a-axis. All the aryl…aryl interactions are in the offset-face-to-face motif, see bottom part of the figure. These interactions between each two centrosymmetric dimers are further supported by weak hydrogen bonds of the type C14–H14B⋯O1 [2.679(1) Å, 152.37(1)°, −x, 1 − y, 1 − z]. Due to the high polarity of the C–F bond, the dimeric supramolecules are also involved in other interactions via two types of F⋯F [2.914(3) Å; C13–F1–F1 106.15(1)°; −x, 1 − y, −z] and Cphenyl–H⋯F [C12–H12⋯F1; 2.562(6) Å; 132.59(1)°; −x, 1 − y, −z] intermolecular interactions, and therefore, the dimeric supramolecules, “aryl embraces”, are largely controlled by fluorine interaction effects, in the c-direction (see bottom part of the figure), forming layers in ac plane. The formed layers (in the ac plane) are interconnected (in the b direction) in a zigzag assembly through C=O⋯H–Cphenyl interactions. Considering these non-classical intermolecular hydrogen bonding and stacking interactions, the molecules are arranged in a 3D extended structure.

Corresponding author: Qutaiba Abu-Salem, Faculty of Science, Department of Chemistry, University of Al al-Bayt, Al-Mafraq 25113, Jordan, E-mail:

Acknowledgments

The authors thank Al al-Bayt University for financial support. We thank late Dr. Abdulaziz Ajlouni for assistance with the NMR measurements, University of Science and Technology, Jordan.

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Conflict of interest: The authors declare no conflicts of interest regarding this article.

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Received: 2025-03-26
Accepted: 2025-04-30
Published Online: 2025-05-07
Published in Print: 2025-08-26

© 2025 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/ncrs-2025-0152
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Hydrothermal synthesis, crystal structure of [K3：N1:N2:N4-3-(pyridin-2-yl)-1,2,4-triazole] binuclear Ni(II) complex[Ni2(C7H5N4)2(C7H4ClO2)2]
  4. The crystal structure of di(thiocyanato-κ1N)-bis(methanol)-di(1,3-bis((pyridin-4-ylthio)methyl)benzene)-iron(II), C40H40FeN6O2S6
  5. Crystal structure of poly[(μ 3-3,3″,5,5″-tetrafluoro-(1,1′:4′,1″-terphenyl)-4,4″-dicarboxylate-κ 3 O,O′:O″)-(μ 4-3,3″,5,5″-tetrafluoro-(1,1′:4′,1″-terphenyl)-4,4″-dicarboxylate-κ 4 O,O′,O″,O‴)-dicadmium(II)]dimethylformamide solvate, C47H30Cd2F8N3O12
  6. The crystal structure of a 3d-4f complex based on 2-(benzo[d]thiazol-2-yl)-6-methoxyphenol C31H27N4O13S2CoEr
  7. Crystal structure of poly[(μ 2-1,4-bis(imidazol-1-yl)benzene-k 2 N:N′)(μ 4-biphenyl-3,3′,5,5′-tetracarboxylic-k 4 O,O,O,O)dizinc(II)] dihydrate, C40H28Zn2N8O9
  8. The crystal structure of 4-(bis(2-chloroethyl)amino)-2-hydroxybenzaldehyde, C11H13Cl2NO2
  9. Synthesis and crystal structure of-(10S,13S,16R,Z) −17-ethylidene-16-hydroxy-10,13-dimethylhexadecahydro-3 H-cyclopenta[α]phenanthren-3-one, C21H32O2
  10. The crystal structure of catena-((μ 2-4,4′-bipyridine-κ 2 N:N′)-bis(4-fluorobenzoato-κ1O)-copper(II)), C24H16F2N2O4Cu
  11. Crystal structure of catena-poly[(ethylenediamine-κ2 N,N′)-μ-tetraoxomolybdato(VI) zinc(II)], C2H8MoN2O4Zn
  12. The crystal structure of 4-chloro-1H-pyrazole-3-carboxylic acid, C4H3ClN2O2
  13. The crystal structure of bepotastine besilate, C27H31ClN2O6S
  14. The crystal structure of (η 6-p-cymene)benzyldiphenylphosphine-diiodido-ruthenium(II) dichloromethane solvate
  15. The crystal structure of poly[(μ 2-1-(1-imidazolyl)-4- (imidazol-1′-yl-methyl)benzene κ 2 N:N′)-(μ 2-3-nitrobenzene -1,2-dicarboxylato-k4,O,O′:O′′,O′′′]zinc(II)-κ 2, C21H15N5O6Zn
  16. The crystal structure of (2R,4S)-5-([1,1′-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methyl pentanoic acid, C23H29NO4
  17. The crystal strucure of [2,2′-{1,2-phenylenebis [(azanylylidene)methanylylidene]}bis(4-fluorophenolato)-κ4 N,N′,O,O′] nickel(II) N, N-dimethylformamide solvate, C23H19F2N3NiO3
  18. The structure of (E)-6-(cyclopropylmethyl)-11-(2,2-difluoropropylidene)-2-methyl-6, 11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C21H21F2NO2S
  19. Crystal structure of catena-poly[(μ 2-(2-(1H-imidazol-1-ylmethyl)benzyl)-1H-imidazole κ2N:N′)- (μ 2-cyclohexane-1,2-dicarboxylato κ2O,O′)cobalt(II) monohydrate]
  20. The crystal structure of 3,5,7-trinitro-1,3,5,7-oxatriazocane
  21. Crystal structure of poly[(μ2-nitrato-κ3 O,O′:O′′)(μ2-1-[(2-propyl-1H-benzimidazole-1-yl)methyl]-1H-benzotriazole-k2 N:N′)silver(I)], C17H17AgN6O3
  22. The crystal structure of (5-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-sulfanylidene-1,3,4-oxadiazol-3(2H)-yl)(3-methylphenyl)methanone, C18H14N2O4S
  23. The crystal structure of diaqua-bis[5-(4-methylphenyl)-1H-pyrazole-3-carboxylato-κ2N,O]-cobalt(II), C11H11Co0.5N2O3
  24. Crystal structure of 2-(6-methoxynaphthalen-2-yl)-N-(4-morpholinophenyl)propanamide, C24H26N2O3
  25. The crystal structure of sodium methylsulfonate
  26. Crystal structure of catena-poly[bis(isothiocyanate κ 1 N)-(μ 2-3,3ʹ-methylenebis(1-methyl-1,3-dihydro-2H-imidazole-2-thione)-κ 2 S:S′)-cobalt(II)], C11H12CoN6S4
  27. The crystal structure of {hexakis(1-methyl-1H-imidazole-κ 1N)nickel(II)} (μ 2-oxo)-hexaoxido-di-molybdenum(VI)─1-methyl-1H-imidazole (1/2), C32H48NiMo2N16O7
  28. 6-(Diphenylphosphoryl)-3,3′,6′-tris(10H-phenoxazin-10-yl)-[1,1′-biphenyl]-2,2′-dicarbonitrile, C62H38N5O4P
  29. The crystal structure of R-2′-amino-N-methyl-N-(1-phenylethyl)-[1,1′-biphenyl]-4-carboxamide, C22H22N2O
  30. The crystal structure of bis{tetrakis(n-butyl)(μ-hydroxy)(2,3,5,6-tetrafluorobenzoate) (μ 3 -oxo)ditin(IV)}
  31. Crystal structure of catena-poly[aqua-(μ 2(3,4-dimethylthieno[2,3-b]thiophene-2,5-dicarboxylato-κ 2 O:O′)-(3,6-bis(4′-pyridyl)-1,2,4,5-tetrazine-κ 1 N)zinc(II)], C22H16N6O5S2Zn
  32. The crystal structure of 3-bromo-5-cyano–N-(5-(cyanomethyl)quinolin-8-yl)pentanamide, C19H15BrN4O
  33. The crystal structure of bis(tetramethylammonium) (di-μ2-aqua)hexaaqua-dibarium(II)) decavanadate
  34. The crystal structure of catena-poly(bis(μ 2-chlorido)- (μ 2-4′-(pyridin-4-yl)-2,2′:6′,2″-terpyridine–N′, N″, N‴:N″″) -chlorido-dicopper(I,II)) monohydrate, C20H16N4OCl3Cu2
  35. Crystal structure of spiropachysine, C31H46N2O
  36. Crystal structure of poly[aqua-(μ 2-3-bromoisonicotinato-κ 2 N: O)-(μ 2-3-bromoisonicotinato-κ 3 N: O: O′)-(μ 3-3-bromoisonicotinato-κ 3 N: O: O′)-(μ 2-nitrite-κ 3 O: O′: O″)dicadmium(II) monohydrate], C19H12Br3Cd2N3O9
  37. The crystal structure of 2-acetylpyridine-ortho-fluoro-phenylhydrazone, C14H12FN3O
  38. The crystal structure of poly(triaqua-(m 2-2,2′-bipyridine-4,4′-dicarboxylato-K 2 O:O′)-bis(m 2-2-2′-bipyridine-4,4′-dicarboxylato-K 4 O,O′:O″:O‴)dierbium(III)) hydrate, C36H26Er2N6O16
  39. The crystal structure of 1,1′-(phenazine-5,10-diyl)bis(heptan-1-one), C26H34N2O2
  40. The crystal structure of (4-([2,2′:6′,2″-terpyridin]-4′-yl)phenyl)boronic acid, C21H16BN3O2
  41. Crystal structure of 6-hydroxy-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione, C6H3N3O3
  42. Crystal structure of N′-((1-hydroxycyclohexyl)(phenyl)methyl)-2-methoxybenzohydrazide ethanol solvate, C23H30N2O4
  43. Crystal structure of pyridinium tetrakis[1,1,1-trifluoro-2,4-pentadionato-K2 O,O′]lutetium(III) C20F12H16LuO8C5H6N
  44. Crystal structure of dichlorido–tetrakis{3-((1H-1,2,4-triazol-1-yl)methyl)-1-(4-chlorophenyl)-4,4-dimethylpentan-3-ol-k 1N}cobalt(II), C64H88O4N12Cl6Co
  45. The crystal structure of tetrakis(4-allyl-2-methoxyphenyl nicotinato-k 1 N)bis(thiocyanato-k 1 N)cobalt(II)
  46. The crystal structure of methyl 4-(3,4-dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C20H21Cl2NO3
  47. The crystal structure of (E)–N-(4-chlorobenzylidene)(4-chlorophenyl)methanamine, C14H11Cl2N
  48. Crystal structure of (E)-4-(4-ethylbenzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, C21H22O4
  49. Crystal structure of 4-bromo-3-nitro-1H-pyrazole-5-carboxylic acid dimethyl sulfoxide monosolvate, C4H2N3O4⋅C2H6OS
  50. Crystal structure of-(1S,4aR,5S)-5,6,7-trihydroxy-8-isopropyl-1-methyl-1,2,3,4,5,10,11,11a-octahydro-4a,1-(epoxymethano)dibenzo[a,d][7]annulen-13-one C20H26O5
  51. Crystal structure of 7,9-dimethoxy-2-methyl-4-propylbenzo[f]isoquinolin-5-yl 4-bromobenzoate, C26H24BrNO4
  52. Crystal structure of bis(N,N,N-trimethylbutanaminium)tridecathiotrimolybdate(2−), (BuMe3N)2[Mo3S13]
  53. Crystal structure of N-(adamantan-1-yl)-4-methylpiperazine-1-carbothioamide, C16H27N3S
  54. Crystal structure of poly[(μ 2-2,2′-[1,4-phenylenebis(methylenesulfanediyl)]dibenzoato-κ 4 O,O′:O″,O‴)-(μ 2-1,1′-([1,1′-biphenyl]-4,4′-diyl)bis(1H-benzimidazole)-κ 2 N:N′)cadmium(II)]dimethylformamide solvate, C51H41N5O5S2Cd
  55. The crystal structure of 2-benzoyl-3′,4′,5′,6′-tetrahydrospiro[isoindoline-1,2′-pyran]-3-one, C19H17NO3
  56. The crystal structure of 1-(4-cyanobenzyl)-4-phenyl-1,4-dihydropyridine-3-carbonitrile, C20H15N3
  57. Crystal structure of (1,3-dioxolan-2-ylmethyl)triphenylphosphonium bromide, C22H22BrO2P
  58. Crystal structure of [(2,4-dichlorobenzyl)triphenylphosphonium] tetrachloridomanganese(II)
  59. The crystal structure of 2-(2-hydroxy-4-n-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, C33H39N3O2
  60. Crystal structure of catena-poly[aqua-(5-carboxypyridine-2-carboxylate-κ 2N,O)(2,5-pyridine-dicarboxylate-κ 4O,O′:N:O″)bismuth(III)], C14H9BiN2O9
  61. Crystal structure of (E)-1-fluoro-4-(2-(phenylsulfonyl)vinyl)benzene, C14H11FO2S
  62. Crystal structure of methyl 2-amino-3-chloro-4-methoxybenzoate, C9H10ClNO3
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